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While most political candidates are fiercely competing for votes against opponents across the aisle, one gubernatorial candidate is fighting in the ring against himself.

In one corner, there’s Charlie Crist, the former Republican governor of Florida with a resume filled with conservative positions. In the other corner, there’s the 2014 Democratic candidate for governor, Charlie Crist, who is running on a left-leaning agenda.

Mr. Crist has been dogged throughout his career about a pattern of major policy shifts for political profit, but critics — in both parties — say the 57-year-old candidate has taken the flip-flopping to another level in hopes of challenging Gov. Rick Scott, a Republican. On issues including abortion, same-sex marriage, gun control and U.S. policy toward Cuba, the candidate now backs positions he once publicly opposed.

“Charlie Crist is the ultimate political opportunist,” said Susan Hepworth, communications director for the Republican Party of Florida. “People can’t trust that what he’s saying now is what he’s going to be saying six months from now. He says whatever is convenient to him at the time. He’s like a finger in the wind; whichever way the wind blows is what he’ll say.”

Mr. Scott’s campaign has run an ad quoting former Vice President Al Gore as saying, “It’s a little unusual to have somebody flip-flop and then flop-flip.”

Florida Democratic Party spokesman Joshua Karp said in an interview that the party would not comment on Mr. Crist’s record or platform this year. He noted that the party has not even had its primary to pick a gubernatorial candidate for November.

“We’re watching the primary unfold,” Mr. Karp said. “There are two Democratic candidates in the running.”

Mr. Crist faced similar charges in his run as an independent for Senate in 2010, when he lost to Republican Marco Rubio.

“Being flexible is not a sin,” he said at the time. “It is frustrating for my partisan opponents to understand that, but that’s really how I am, and I think that’s how most of Florida is.”

Asked about this year’s flip-flopping charges, a Crist representative said, “Gov. Crist has always put the people of Florida ahead of partisan politics. Like many Americans, he doesn’t believe there is just one answer to every issue, and he will always land on the side of the middle class, because he knows Floridians want a governor who will work with both parties, not just engage in rank partisan bickering.”

Still, Mr. Crist has given his opponents plenty of ammunition over the years.

In 2006, Mr. Crist told The Associated Press that he would sign a bill to ban abortion if it came across his desk. But while he was governor in 2010, he vetoed a bill that would have made abortions more difficult to obtain.

In 2005, Mr. Crist told state reporters that he supported a ban on same-sex marriage. But last year, he advocated for marriage equality, adoption rights and protection against employment discrimination, and he apologized for his previous positions on same-sex marriage, according to Watermark Online.

Mr. Crist went on record in support of a 2008 proposal by Sen. John McCain, Arizona Republican, to lift a ban on offshore drilling. But two years later as governor, Mr. Crist called a special legislative session to consider a ban on offshore drilling.

Most recently, Mr. Crist appeared to reverse his opinion on the U.S. embargo with Cuba, a political hot potato in Florida. In an interview with Bill Maher on HBO’s “Real Time,” Mr. Crist said “we need to get the embargo taken away.”

Mr. Maher noted, “I don’t see a lot of politicians from Florida that have the courage to stand up to that small Cuban community.”

As the audience applauded, Mr. Crist responded, “Well, I think we need to. I think it’s the right thing. The embargo has been there for 50 years now? I don’t think it worked.”

That contrasts with Mr. Crist’s 2010 Senate run, when he was much more amenable to the embargo. He told reporters from the South Florida Sun-Sentinel that he would not favor less restriction on travel between the U.S. and Cuba “until they offer freedoms to their own people first and demonstrate that they’re serious about that.”

No issue has inspired more policy flexibility from Mr. Crist than President Obama’s health care law. Mr. Crist told the AP on the night after the House passed the Affordable Care Act in March 2010 that he would work to repeal Obamacare if elected to the Senate.

But in July 2010, he told The Wall Street Journal that he did not support a repeal of the law.

Nine days later, he released a statement saying: “Recent reports in the media have confused my position on the Obama health care bill. The Obama health care bill was too big, too expensive, and expanded the role of government far too much. Had I been in the United States Senate at the time, I would have voted against the bill.”

Then on Aug. 27, 2010, Mr. Crist told a local Orlando news anchor, “I would have voted for [Obamacare], but I think it can be done better. I really do.”

Two hours later, Mr. Crist said he misspoke and wanted to repeal Obamacare.

Then, two days later, Mr. Crist avoided giving a clear response in a CNN interview. “Well, whatever word you want to use, what we need [is] to fix it, and we need to go forward. This is about what’s doing right for the people.”

In October 2010, Mr. Crist was back to his old stance. “Obamacare was off the charts, was wrong,” he told the AP.

Fast-forward to November 2013, and The Naples Daily NewsMakers reported that Mr. Crist once again claimed to support Obamacare.

Whether Mr. Crist’s record will sink him in the election remains an open question. Early polls show him with a slight lead over Mr. Scott, including a University of Florida poll in late January that gave the Democrat a 7 percentage point lead. Some 55 percent of Floridians in that poll rated Mr. Crist “honest and ethical,” compared with 51 percent for Mr. Scott.

Mr. Crist also has cited popular former Florida Gov. Jeb Bush, a Republican, to justify his own party switch. He said the Republican Party changed positions as it moved to the right in recent years. Political observers are uncertain whether that argument will work.

“The voters will give him a pass if they believe that he is being true to his beliefs by running as a Democrat, if [voters] believe that the Republican Party has gone so far right that he had no other way,” said Bill Burges, president of Burges & Burges Strategists, a nonpartisan political consulting firm.